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Paper | Special issue | Vol 90, No. 2, 2015, pp.950-966
Published online, 7th August, 2014
DOI: 10.3987/COM-14-S(K)63
Enantiodivergent Synthesis of Wieland-Miescher Ketone Analog Mediated by a Chiral Pyridinylmethylamine Derivative

Shota Honda, Kohei Inomata,* and Yasuyuki Endo*

*Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


A new enantiodivergent route to provide the Wieland-Miescher ketone analog (3b) bearing a 7-membered ring via the intramolecular aldol reaction of the trione (5) mediated by a single chiral pyridinylmethylamine derivative (13e) was established. Although the enantioselectivities of 3b were moderate, the complete inversion of the enantioselectivities was observed based on the amount of additional trifluoroacetic acid (TFA). The basicity of the nitrogen atom on the pyridine ring was very important for this enantiodivergent behavior.